


Tumblr Drabbles

by xxenjoy



Category: Supernatural
Genre: M/M
Language: English
Status: In-Progress
Published: 2015-05-25
Updated: 2019-06-03
Packaged: 2019-09-14 15:21:27
Rating: Not Rated
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 6
Words: 5,095
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/16915395
Author URL: https://archiveofourown.org/users/xxenjoy/pseuds/xxenjoy
Summary: A collection of random drabbles from Tumblr.





	1. Through the Years

**Author's Note:**

> Who knows how long NSFW written content will last over there, so I'm cross-posting to preserve anything I don't already have saved.  
> It took everything in me not to re-edit the old things. Apologies for any mistakes, I'm catching the minor ones as I go, but I might miss some.
> 
> Each chapter will be rated separately and any warnings will be posted in the author's notes.   
> Tags should be updated soon!

|| rating: G

For Castiel Novak, elementary school is when he discovers he’s gay. He doesn’t know that’s what it is when it happens, but when Dean Winchester transfers in from Kansas, he’s the most beautiful person Cas has ever seen. Dean’s a little quiet at first, but at the year progresses, he adjusts to his new surroundings and comes into himself. He’s maybe not the best behaved, but he’s hilarious and everyone loves him - teachers and students alike. Cas’ friends tease him about his obvious crush, and tell him he should just go say hi to Dean, go show him his Star Wars lunch box because they saw Dean wearing a t-shirt with Han Solo on it the other day. Cas plays through dozens of these situations in his head, but ultimately is always too shy to go and talk to him, so he continues to sit off to the side and laugh quietly along with everyone else.

\- - -

Middle school is a rough time for Dean. His little brother is in the same school as them now, and the pair of them get pulled out one day near the beginning of the year and nothing is right again after that. Cas knows it’s something to do with Dean’s dad - his Mom passed away when they were just kids - because his friend Benny knows Dean, but he doesn’t ask more than that because he knows it’s none of his business. He does, however, shut down every incorrect rumor that he hears, because he knows things are hard for the Winchester boys and the last thing either of them needs is false stories tangling together and making a mess.

Dean is strong though, and he pushes through it, a smile on his face and a joke on his lips whenever there are people around. Cas has seen him break down though, once, behind the school while he was talking to someone one the phone, and ultimately chucked his phone over the fence and slid down the side of the building with his head in his hands. Cas had wanted so badly to go to him and ask if he needed anything, but Dean was back there for a reason. He didn’t want anyone to see him, and Cas would respect that, regardless of how much it hurt to just leave Dean on his own like that.

By their final year, Sam and Dean have both perked up again, and Dean is drowning in people who want to go to their grade nine graduation dance with him. Dean’s never said anything about his sexuality, but it’s widely assumed that he’s bisexual, though even with that information, Cas can’t bring himself to go and ask him. Dean has his choice of just about anyone in school, and Cas knows he can’t compare to that, so he throws himself into studying for his exams and winds up going to graduation with his best friend Anna.

\- - -

If he thought Dean was popular in middle school, it’s nothing compared to high school. Every single person at that school loves him, except maybe Gordon Walker. Dean’s captain of the football team, and although he’s now openly bisexual, has very few problems with anyone but the opposing teams. He spends most of his final year with Lisa Braeden, the head cheerleader, and most people think they’re dating, but because Cas had befriended Charlie Bradbury, and she refuses to let go of her whole Dean and Cas fantasy, he knows the pair of them are just friends and Lisa’s actually more interested in Victor Henrikson.

There are parties every weekend, and although Anna and Charlie are insistent that Cas go, he stays home most night with his books or Lord of the Rings. All high school parties are is drinking too much, telling people things you wish you hadn’t, and having semi-public sex while you’re too drunk to remember it the next day. No one wants to have sex with him, and he’d rather not blurt out any drunken confessions, so he stays at home and lives vicariously through his two best friends.

\- - -

Somehow, Dean and Cas end up at the same college, even though Cas chose to stick close to home, and he knows Dean could have done so much better. At this point, he’s starting to wonder if his feelings for Dean will ever go away, and he’s debated more than once asking Sam to introduce them. They’ve spoken a few times - you don’t go to school with someone your whole life and never talk to them - but they could barely even be considered acquaintances, and Sam and Cas have become pretty good friends over the last few years, especially since Sam started dating Anna’s sister Ruby.

Dean is still loved by everyone he sees, though Cas isn’t surprised in the least. He still goes to all the parties and manages to get amazing grades despite it, and though Cas does increasingly well in school, he can’t help but be a little jealous because he works himself to the bone while Dean just seems to soar through.

In December, a lot of kids end up staying on campus, and there’s a New Year’s party for anyone who’s there. Because it’s Christmas break, and he really has nothing better to do, Cas lets Charlie drag him along with her. The party’s in a little hippy cafe with booze and snack and way-too-loud music, and Cas is a little uncomfortable so he sits near one of the windows, gazing out at the beach and wondering what Dean is doing over the holidays.

He doesn’t have to wonder long. He’s only been sitting for a few minutes when there’s the scrape of a chair and Dean Winchester sits down across the table, looking like he’s trying not to smile.

“What do you want?” Cas asks, and then instantly feels like an idiot for sounding so rude.

“Don’t be like that, Cas, I just wanted to- no, you’re right, never mind.” He moves to push his chair back and Cas wants to shoot himself for managing to fuck this up because he can’t control the words coming out of his mouth. He does the first thing he thinks of and grabs Dean’s hand, effectively stopping him, and then yanks his hand back, blushing hard when he realizes what he just did.

“Dean, wait. I didn’t mean for that to come out like that. Um, what did you want to say?”

Dean’s demeanor changes immediately and he looks down at the ground, “I just wanted to ask if maybe you’d wanna dance?” his voice rises anxiously at the end up and looks up at Cas uncertainly.

“What?” Cas asks stupidly, and Dean reaches out, taking his hand again.

“Dance with me?”

Cas nods silently and lets himself be led away from the table, his mind struggling to catch up to the situation. Dean’s arm circles around his waist, and it’s remarkably easy to melt into him, his arms coming up around Dean’s neck as they move slowly as one.

“You know,” Dean says softly, leaning in so their heads bump together, “I wanted to ask you out since sixth grade.“

"What?” Cas blurts, and Dean chuckles softly, sliding one hand up Cas’ side to tilt his chin up.

“I was afraid you’d say no because we’re so different, and I didn’t want to hear you say no.” Cas shakes his head minutely, biting the inside of his lip to keep from smiling like the giant dork that he is.

“You were wrong,” he says simply.

“What?”

“I wouldn’t have said no.”

“You- really?”

“Really,” Cas breathes, and it takes all his effort not to close the space between them and press his lips against Dean’s.

“Then would you-”

Cas’ face breaks into a grin and his restraint breaks, his hands sliding up into Dean’s hair to pull him closer. Their lips press together and it only takes Dean a second to get over the surprise, before his arms tighten around Cas, his mouth hot as he kisses back without restraint. Cas only breaks away to breathe.

“Yes,” he hums as he pulls away.

Dean chuckles softly, “you don’t even know what I was going to say.”

“Doesn’t matter,” Cas smiles, bumping his nose against Dean’s, “the answer is yes.”


	2. Author!Cas

|| rating : M

okay but Dean and Cas who were lovers when Dean was living abroad and Cas was struggling to write his first novel. only ten years later they run into each other again and Cas is famous for his writing and Dean can’t believe his luck running into him on the sidewalk.

But Cas is bombarded by a horde of fans before he and Dean get a chance to talk, and then his driver shows up so he grabs Dean’s hand and pulls him into the car with him and they finally get a chance to catch up as they drive back to the hotel. Cas is supposed to be at a book signing, but he has about an hour and neither of them wants to leave, so he drags Dean into the elevator with him and it’s the first time they’ve been alone and the tension is palpable. one of them makes a joke, but it falls flat and then there are two seconds of dead silence before they’re all over each other and by the time the elevator reaches Cas’ floor, they’re half-dressed and panting. 

Dean follows him back to his room and Cas shuts the door and pushes him onto the bed and proceeds to spend the next hour fucking him senseless, and everything comes out. how Dean never wanted to leave, how Cas very nearly dropped everything to follow him back to the states and Dean kisses him like it’s the first time and the last time and he struggles to keep up because Cas is just so. damn. good. at everything he does, but then it’s five minutes until Cas is supposed to be at his signing and someone is banging on the door and Cas laughs as he drags himself out of bed, kissing Dean and promising to finish what he started and he’s still hard in his jeans as he heads down to the conference room, leaving Dean to get dressed on his own, which he does, taking great care to make himself look extra hot.

And he goes down and there are hundreds of people waiting to see Cas and he can overhear these two girls absolutely dying over Cas and talking about how he looks like he’s just crawled out of bed and how it’s a good look on him, and Dean is just so smug as he strolls past because he’s the reason Cas looks like that and he is so damn proud that he buys a book and jumps into the line, and when he gets to Cas he just winks and goes ‘sign my book?’ and Cas just looks at him, and writes something absolutely filthy because Dean is too damn smug. and Dean just gapes at him as he steps aside, and Cas winks before moving on and totally ignoring him. but then later, when Cas is finally done and exhausted, he goes back to his hotel room to find Dean waiting for him in his bed.


	3. Pride Parade

|| rating: G

 

Picture this

Cas and Dean are best friends and Cas is totally upfront about everything he feels and he’s outgoing and outspoken, but Dean keeps to himself and just kind of gets by. But Cas is always up there at the front lines whenever there’s a rally or a protest he believes in - gun control, women’s marches, gay rights - he’s always RIGHT THERE leading the way with body paint and banners and a megaphone. And Dean’s got so much shit going on or he would be there to support him, because he’s so damn proud of his best friend because Cas is just SO GOOD and he’s working to change the things that are wrong with this godawful world. And Dean loves him so much, more than he can cope with, but he can’t do anything about it because he’s not out - not even Cas knows he’s bi. So he just sits and loves him quietly from the sidelines and helps him paint his posters or his chest, or whatever it is that he’s painting that day, and wishes him luck as he heads out, desperately wishing he could kiss him goodbye. And he watches the rallies on TV from work just to catch a glimpse of him while he’s doing whatever it is he’s doing that day.

But the Pride rolls around and it’s already the hardest time of the year for Dean because he wants to be part of it, but he’s not brave enough to share his sexuality with the world. Only then he’s at work, and they’re showing footage of the parade at work. And some fucker comes in and starts shitting all over it because homosexuality is wrong and they’re all going to burn in hell. And Dean does his best to keep himself calm because he can handle people badmouthing him, but that’s Cas out there marching in that parade, and Dean’ll be damned if he lets someone say this shit about Cas. So he comes out from behind the counter and tells the guy to get out, but then he starts calling Dean all sorts of shit. And he takes it, because he’s at work, but the guy steps over the line when he starts badmouthing ‘your fucking boyfriend’ and he punches the guy. In the same breath, he’s punched a customer in the face, ripped off his work shirt and he’s out the door, running blindly.

And when he gets where he’s heading, when he finds the parade, there are so many people everywhere that he’s overwhelmed but then one voice rises above the rest and he smiles to himself as he follows the sound. And when he finds Cas, he’s surrounded by people. With his stupid megaphone and his stupid rainbow chest and he’s absolutely beaming when he sees Dean. And Dean just takes his hand and tells him he loves him. And Cas just stops and hands off his megaphone. And kisses him. And Dean melts into him, and it’s the happiest he’s ever felt. And they just stay like that, for ages, wrapped around each other while everyone else continues around them.


	4. Massage Therapy

**Notes for the Chapter:**

> Dom!Cas/Sub!Dean

||rating: E

Cas is a massage therapist and normally he’s really good with his clients, but one day Dean comes in (after being forced to go by Sam bc his back has been bugging him) and right from the beginning Cas is thrown off because Dean is hot and friendly and super chatty and most of the time his clients just shut up and let him get on with it. Dean does, but then when they get into the room, he takes off his shirt and every damn inch of his skin is covered in freckles and Cas has to turn away to keep from staring at him as he strips. So he sets himself to turning on the music and explains to Dean what he’ll be doing and when Dean lies down, Cas focuses himself and gets to work.

Only Dean isn’t quiet when Cas hits a sweet spot, and it’s killing him because he was never trained how to deal with his clients moaning under his hands - it does happen occasionally, but Dean is taking it to another level and when Cas apologizes for any pain, Dean just jokes that he likes the pain (a vain attempt to make it less uncomfortable) and it takes every ounce of Cas’ restraint not to comment on that and when he asks him to turn over Dean makes a sheepish sort of laughing sound and asks for a couple of minutes alone. Cas knows he’s hard and he just leaves without saying anything because if he does say anything, he’s sure to regret it so he goes and sits in the other room for a minute to calm down, and when he goes back and knocks on the door again, Dean says he’s ready so Cas goes in to finish up and he’s never been so thankful to get anyone off his table before in all the years he’s been doing this.

And while they’re finish up with payment and booking Dean in again (fuck his actual life) Dean makes a comment about that being the best massage he’s ever had and Cas, forgetting that he’s not quite out of the woods yet, instinctively laughs and says “no, buy me a drink and I’ll show you the best massage you’ve ever had” and for a second he’s mortified because holy shit this is inappropriate and obviously Dean understands the implications, but Dean doesn’t skip a beat before asking if he’s free tonight and Cas is thankful that it’s only the two of them here, because if anyone else was in the centre right now, he’d never live down agreeing to see a client outside of work - for drinks, no less - but he does agree and Dean leaves with a giant grin on his face, though not after not-so-subtly slipping Cas his number.

Cas has three more appointments that he barely makes it through thinking about what’s going to happen tonight, and then he goes home and texts Dean while he gets ready. Dean texts him an address and despite everything in him telling him he’s an idiot for agreeing to this, Cas meets him at the bar because Dean is hot and Cas hasn’t done anything fun in forever. When he gets there, Dean’s sitting at the bar in a pair of tight jeans and an even tighter shirt and Cas would fuck him right there on the bar if it wouldn’t get them kicked out - or worse.

So he goes over and Dean is very obviously checking him out - much to the apparent disappointment of the bartender he was chatting with a second ago - and Dean buys him a drink and they sit and chat. Cas relaxes after a little while and forgets how they ended up here because Dean is actually really funny and sweet and it’s doing nothing to dissuade him from doing something that will get them both arrested. After a little while, Dean pauses and turns to look at him all “so about that massage” and Cas makes a joke like “we probably shouldn’t do that here” and Dean slips off his stool and gets right up in his space and suggests they get out of here then.

So they head back to Cas’ because he has a legit massage table at home, only once they get there, Cas leaves Dean alone for five seconds and when he comes back, Dean’s smirking at him with a pair of leather cuffs in his hands. Cas struggles to come up with a good excuse, but Dean just walks over and asks if he ties down all his clients and Cas bites and stares him dead in the eyes and says “only if I need to.” Dean doesn’t say anything, but he doesn’t look away and when Cas asks if he wants to be cuffed, Dean just nods slowly and it’s so fucking hot, how could he say no?

So Cas asks Dean to strip down as much as he’s comfortable and when he turns back Dean’s wearing nothing but a pair of silk panties and he should have known Dean wasn’t going to make this easy for him. He gets Dean up on the table but it’s there’s not enough space to cuff him, so against Cas’ better judgment they move to the bedroom. Dean is fucking thrilled to find Cas’ bed is one of those fancy ass four-posters and while he gets on the bed Cas pulls out a whole different set of cuffs and cuffs his hands to the bed while mumbling about coming here for a massage table, but Dean doesn’t seem to mind one bit and when he cuffs his ankles, Dean wiggles in place and it’s all Cas can do to keep himself in check so he gets the stuff from the cupboard and puts on some music (Led Zeppelin bc he thought Dean might appreciate it more than the ambient whatever).

So he climbs up over Dean he asks what he wants and Dean just responds with “anything you want, baby, my body’s yours” and Cas is stupid enough to just keep going, but he starts out simply, just working on his back, but Dean squirms and moans and pushes his ass up until Cas gets fed up and presses him down against the bed and he can hear the gasp before Dean freezes and when Cas mutters “stay still” and Dean does. And he doesn’t move, though when Cas moves down to his thighs, Dean shudders and groans into the bed and it doesn’t take a genius to realize that Dean’s thighs are insanely sensitive and since Dean’s been a brat this whole time Cas takes full advantage of this knowledge before moving back up to his back, running his hands over Dean’s ass.

And he’s so careful, touching him so specifically, and he knows Dean wants him and it’s starting to get to him and when he asks “can I do something?” Dean immediately agrees, breathlessly. When Cas’ fingers slip under the edge of his panties, his hips twitch just a little, until Cas presses them down again but then he stops and Dean turns to look back at him, and Cas pulls on the hem of the panties tugging them down over his ass. He’s careful about undoing Dean’s ankles and taking the panties off so they don’t get covered in oil and then he cuffs him again.

And Dean loves it when Cas massages his ass, groaning and mumbling into the pillow and he starts rambling about how good it feels and asking for more and Cas switches gears really quickly telling him to be quiet and when he doesn’t shut up, Cas threatens to gag him and Dean just groans more and still doesn’t stop. So Cas gags him, giving him a hand gesture to use if he wants him to stop and Dean nods his understanding before Cas goes back to work.

It’s difficult, bc Cas is hard just thinking about all the things he wants to do to him, but he doesn’t want Dean to know that, so he does his best to keep away from him, settling between Dean’s legs as he keeps going massaging his legs and back up to his ass and when he slips between his cheeks Dean whimpers and his hips jerk back and Cas shoves him back down and smacks him instinctively, and he freezes, but Dean is still and doesn’t make any attempt to stop him so he keeps going, trying to figure out how the hell he ended up here.

And when he presses his thumb against Dean’s hole he gets almost no reaction, so he leans down next to Dean’s ear and tells him he can make noise so long as he doesn’t talk and asks if he understands and Dean nods with a little whimper and Cas presses against him again. And as he presses deeper, Dean struggles to keep still, but it doesn’t take much to remind him who’s in charge this time and Cas is riding the high and by the time he gets his own cock out, Dean’s an absolute mess under him, panting and whimpering and Cas loves him like this.

So he leans over Dean again, letting his cock settle against Dean’s ass and whispers in his ear how fucking good he looks like this, how he should see himself all trussed up and aching to be fucked, and when he asks if Dean wants his cock, he may not be able to speak but Dean’s response is abundantly clear. But Cas pulls away and teases him for ages, rubbing his cock against Dean’s ass and his thighs, and when he finally pushes in, Dean’s whole body relaxes around him and he tells Dean not to come on the bed and Dean nods.

Cas fucks him slowly, letting Dean feel every inch of his cock before pulling out and uncuffing him from the bed. Dean gives him a look, but Cas knows what he’s doing and it’s obvious that Dean trusts him so he links Dean’s wrists together and pulls Dean up into his lap so his arms loop backward around Cas’ neck. It’s an awkward position, but Dean doesn’t seem to mind, and when Cas presses into him again, Dean arches off of him with a moan.

And when they’re done, after Dean has come twice and Cas gives in to the coiling heat in his gut, Dean is totally limp, rolling over and flopping onto Cas’ chest. Cas kisses him slowly before hauling Dean up off the bed and carrying him into the bathroom to get cleaned up. And once they’re clean and Cas can breathe again, he puts Dean to bed and finds a movie for them to watch and a blanket that’s not covered in oil and pre-come. Dean is much less cocky when he’s been fucked stupid, and Cas decides that maybe this wasn’t the stupidest decision he ever made - especially when he wakes up to Dean’s mouth wrapped around his cock.


	5. 14x08

**Notes for the Chapter:**

> Minor spoilers for s14 episode 6

||rating: G

Things go on, but Cas never forgets because it’s always there in the back of his mind, creeping up on him and then one day it happens, and idk how but Dean tells him how he feels - lays it all out there, but instead of being happy Cas is devastated because this means he’ll never see Dean again  
or Sam  
or Jack  
or anyone  
but nothing happens and so he tells Dean he loves him too, just as aware that it could all be over in seconds, but Dean deserves to know. Only still, nothing happens because right now  
all he feels is guilt and misery that Dean can finally say these things and now Cas will be gone. Only he’s not, and days go by  
then weeks  
and months  
and Cas is skeptical, but he doesn’t focus too much on it. Instead, he treats every moment with Dean like the last, fearing that it will be. Until one day, months down the line, he realizes how long it’s been and that the empty still hasn’t come to claim him and that maybe he /can/ be with Dean. And that’s the turning point - when fear and guilt and anxiousness turn to happiness, and that’s the moment when the empty comes for him


	6. College au

imagine teenage Cas (we’ll say he’s 19, so college au) and at school he’s a huge dork and he loves his classes and he’s kind of an outcast, but jock!Dean finds these videos of him online one day and can’t fucking believe what he’s seeing bc sweet and innocent pastor’s son Castiel is actually not at all innocent. And he doesn’t mean to, but he gets off on the videos and maybe the next time he actively seeks them out. And then at school a few days later he runs into Cas who is just trying to avoid him bc he’s a nerd and Dean’s a jock and that’s a bad combination, but Dean stops and asks him about the videos and Cas thinks he’s going to try and blackmail him or smth but Dean is just so soft and awkward that Cas gives him a chance and Dean explains that he watches the videos and that they were really good and he’s bright red and Cas doesn’t know what to do and Dean admits that he was wrong about him and that Cas isn’t just a boring dork. And they get interrupted by the bell or one of Dean’s friends or something and he doesn’t get to finish what he was going to say.

But Cas thinks about it a lot and after not seeing Dean for a couple of days, he leaves messages in his locker with his phone number or smth saying if you want to get to know the real me I’m free Wed and Fri after class. So Dean and Cas become friends (secretly ofc bc they don’t fit in the same social circles) but secretly Dean likes Cas more than his other friends bc he’s more genuine and he doesn’t make fun of Dean for liking Star Wars. And then one time Dean goes to Cas’ room and Cas is naked on his bed with the camera set up and Dean asks if he’s streaming but Cas says he’s only filming and he tells Dean he can watch if he likes, so he does

And Cas tells him he can touch himself if he wants to and Dean does but he just rubs his dick through his pants bc he’s still kind of shy bc Cas is beautiful naked. But then Cas calls him over to the bed and Dean listens and climbs up across from him and Cas asks if it’s okay if he undoes his pants. And it’s definitely okay but Dean doesn’t know how to tell Cas that he’s a virgin and all of this is new to him, so Cas gets his pants undone and Dean’s already hard and there’s no hiding it now so Cas asks if he can just and Dean just goes quiet so Cas says he can touch him if he wants to and Dean tells him he’s never touched another guy’s dick before and Cas assures him that it’s okay. So Dean lets Cas touch him too and he Cas gets him out of his jeans and tells him he has such a nice dick and Dean doesn’t know what to say so he squirms but the second Cas’ mouth wraps around him he can’t shut up bc it’s so fucking good only the pressure just keeps building and building and doesn’t stop and suddenly Dean’s acutely aware that he’s about to come and doesn’t even have time to warn Cas before he’s coming down his throat. He’s totally embarrassed about it, but Cas just pulls off of him and lies him down on the bed before crawling over him and jerking off on his chest.


End file.
